Cruising Sailors of St. Michaels is a community of sailors invested in safe, community cruises. Members must own a sailboat in the Talbot County area and commit to a minimum of two cruises of at least six nights over two years. Cruises typically are within the waters of the Chesapeake; however, the Cruising Sailors have ventured as far south as North Carolina. The Cruising Sailors host social events throughout all seasons.